2.0 2012-05-31 14:00:14 -0600 2015-06-03 15:54:31 -0600 ECMDB03712 M2MDB000522 (2E)-Dodecenoyl-CoA (2E)-Dodecenoyl-CoA is an intermediate in fatty acid metabolism, the substrate of the enzyme acyl-CoA oxidase [EC-1.3.3.6], and enzymes acyl-CoA dehydrogenase, long-chain-acyl-CoA dehydrogenase [EC 1.3.99.3-1.3.99.13]. It is also an intermediate in fatty acid elongation, being the substrate of the enzyme enoyl-CoA hydratase and [EC 4.2.1.17]. (KEGG) (2<i>E</i>)-dodec-2-enoyl-CoA (2<i>E</i>)-dodecenoyl-CoA (2E)-Dodec-2-enoyl-CoA (2E)-Dodec-2-enoyl-Coenzyme A (2E)-dodecenoyl-CoA 2-trans-Dodecenoyl-CoA 2-trans-Dodecenoyl-Coenzyme A <i>trans</i>-dodec-2-enoyl-CoA Trans-Dodec-2-enoyl-CoA C33H52N7O17P3S 943.789 943.235323499 {[5-(6-amino-9H-purin-9-yl)-2-[({[({3-[(2-{[2-(dodec-2-enoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid [5-(6-aminopurin-9-yl)-2-{[({3-[(2-{[2-(dodec-2-enoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid 1066-12-2 CCCCCCCCC\C=C\C(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)([O-])OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(=O)([O-])[O-])N1C=NC2=C1N=CN=C2N InChI=1S/C33H56N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-24(42)61-17-16-35-23(41)14-15-36-31(45)28(44)33(2,3)19-54-60(51,52)57-59(49,50)53-18-22-27(56-58(46,47)48)26(43)32(55-22)40-21-39-25-29(34)37-20-38-30(25)40/h12-13,20-22,26-28,32,43-44H,4-11,14-19H2,1-3H3,(H,35,41)(H,36,45)(H,49,50)(H,51,52)(H2,34,37,38)(H2,46,47,48)/p-4/b13-12+/t22-,26-,27-,28+,32-/m1/s1 IRFYVBULXZMEDE-DEEZISNZSA-J Solid Cytosol logp 1.41 ALOGPS logs -2.61 ALOGPS solubility 2.30e+00 g/l ALOGPS logp -0.95 ChemAxon pka_strongest_acidic 0.82 ChemAxon pka_strongest_basic 4.01 ChemAxon iupac {[5-(6-amino-9H-purin-9-yl)-2-[({[({3-[(2-{[2-(dodec-2-enoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid ChemAxon average_mass 943.789 ChemAxon mono_mass 943.235323499 ChemAxon smiles CCCCCCCCC\C=C\C(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)([O-])OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(=O)([O-])[O-])N1C=NC2=C1N=CN=C2N ChemAxon formula C33H52N7O17P3S ChemAxon inchi InChI=1S/C33H56N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-24(42)61-17-16-35-23(41)14-15-36-31(45)28(44)33(2,3)19-54-60(51,52)57-59(49,50)53-18-22-27(56-58(46,47)48)26(43)32(55-22)40-21-39-25-29(34)37-20-38-30(25)40/h12-13,20-22,26-28,32,43-44H,4-11,14-19H2,1-3H3,(H,35,41)(H,36,45)(H,49,50)(H,51,52)(H2,34,37,38)(H2,46,47,48)/p-4/b13-12+/t22-,26-,27-,28+,32-/m1/s1 ChemAxon inchikey IRFYVBULXZMEDE-DEEZISNZSA-J ChemAxon polar_surface_area 363.63 ChemAxon refractivity 219.34 ChemAxon polarizability 91.59 ChemAxon rotatable_bond_count 29 ChemAxon acceptor_count 17 ChemAxon donor_count 9 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon Fatty acid metabolism This pathway depicts the degradation of palmitic acid (C16:0). Fatty acid degradation and synthesis are relatively simple processes that are essentially the reverse of each other. The process of fatty acid degradation, also known as Beta-Oxidation, converts an aliphatic compound into a set of activated acetyl units (acetyl CoA) that can be processed by the citric acid cycle. An activated fatty acid is first oxidized to introduce a double bond; the double bond is then hydrated to introduce an oxygen; the alcohol is then oxidized to a ketone; and, finally, the four carbon fragment is cleaved by coenzyme A to yield acetyl CoA and a fatty acid chain two carbons shorter. If the fatty acid has an even number of carbon atoms and is saturated, the process is simply repeated until the fatty acid is completely converted into acetyl CoA units. Fatty acid synthesis is essentially the reverse of this process. Because the result is a polymer, the process starts with monomers—in this case with activated acyl group and malonyl units. The malonyl unit is condensed with the acetyl unit to form a four-carbon fragment. To produce the required hydrocarbon chain, the carbonyl must be reduced. The fragment is reduced, dehydrated, and reduced again, exactly the opposite of degradation, to bring the carbonyl group to the level of a methylene group with the formation of butyryl CoA. Another activated malonyl group condenses with the butyryl unit and the process is repeated until a C16 fatty acid is synthesized. The first step converts the hydroxydecanoyl into a trans 2decenoyl acp through a protein complex conformed of a hydroxomyristoyl dehydratase and a hydroxydecanoyl dehydratase. The second step leads to the production of a cis 3 decenoyl acp through a 3-hydroxydecanoyl acp dehydratase. For the third step the cis 3 decenoyl acp enters a cycle involving a synthase, reductase, dehydratase and an enoyl reductase which in turn produce a cis x enoyl-acp, hydroxy cis x enoyl, trans x-2 cis x enoyl acp and cis x enoyl respectively.This is done until a palmitoleoyl is produce. In said case the pathway procedes in two different directions. It can either produce a palmitoleic acid through a acyl-coa thioesterase, or produce a Vaccenic acid through a different set of reactions. This process is achieved through a 3-oxoacyl acp synthase, a 3-oxoacyl acp reductase, a 3r hydroxymyristoyl dehydratase and an enoyl acp reductase that produces a transition through 3-oxo cis vaccenoyl acp, 3 hydroxy cis vaccenoyl acp, cis vaccen 2 enoyl acp and a cis vaccenoyl acp respectively. At this point it goes through one final reaction to produce a Vaccenic acid, through an acyl-CoA thioesterase PW000796 ec00071 Metabolic fatty acid oxidation (laurate) Although enzymes of the pathway handle both short and long chain fatty acids, it is the long chain compounds that induce the enzymes of the pathway . Each turn of the cycle removes two carbon atoms until only two or three remain. When even-numbered fatty acids are broken down, a two-carbon compound remains, acetyl-CoA. When odd number fatty acids are broken down, a three-carbon residue results, propionylCoA. Unsaturated fatty acids, with cis double bonds located at odd-numbered carbon atoms, enter the main pathway of saturated fatty acid degradation by converting related metabolites of cis configuration and D stereoisomers, derived from breakdown of unsaturated fatty acids, to the trans- or L isomers of saturated fatty acid breakdown by an isomerase and an epimerase, respectively. When cis double bonds are located at even-numbered carbon atoms, such as linoleic acid (cis,cis(9,12)-octadecadienoic acid), after the fatty acid is degraded to the ten carbon stage an extra step is required to deal with the resulting compound, trans,δ(2)-cis,δ(4)decadienoyl-CoA. The enzyme 2,4-dienoyl-CoA reductase, converts this to trans,δ(2)decenoyl-CoA which enters the normal cycle at the point of the isomerase. The order of the reaction is as follows: a 2,3,4 saturated fatty acid is transformed into a 2,3,4 saturated fatty acyl CoA through a Long and short chain fatty acid CoA ligase. The 2,3,4 saturated fatty acyl CoA is then transformed into a trans 2 enoyl CoA. This enoyl can also be produced from a cis 3 enoyl CoA through a fatty acid oxidation protein complex. The trans 2 enoyl is transformed into a 3s 3 hydroxyacyl CoA through a 2,3 dehydroadipyl CoA hydratase. This same enzyme turns the product into a 3-oxoacyl-CoA. This is followed by the last step in the reaction when the oxoacyl-coa is turn into an acetyl coa+ a 2,3,4 saturated fatty acyl CoA through a 3-ketoacyl-CoA thiolase PW001020 Metabolic Specdb::NmrOneD 10642 Specdb::NmrOneD 10643 Specdb::NmrOneD 10644 Specdb::NmrOneD 10645 Specdb::NmrOneD 10646 Specdb::NmrOneD 10647 Specdb::NmrOneD 10648 Specdb::NmrOneD 10649 Specdb::NmrOneD 10650 Specdb::NmrOneD 10651 Specdb::NmrOneD 10652 Specdb::NmrOneD 10653 Specdb::NmrOneD 10654 Specdb::NmrOneD 10655 Specdb::NmrOneD 10656 Specdb::NmrOneD 10657 Specdb::NmrOneD 10658 Specdb::NmrOneD 10659 Specdb::NmrOneD 10660 Specdb::NmrOneD 10661 Specdb::MsMs 1258348 Specdb::MsMs 1258349 Specdb::MsMs 1258350 Specdb::MsMs 1373500 Specdb::MsMs 1373501 Specdb::MsMs 1373502 Specdb::MsMs 2274183 Specdb::MsMs 2274184 Specdb::MsMs 2274185 Specdb::MsMs 3091708 Specdb::MsMs 3091709 Specdb::MsMs 3091710 HMDB03712 5280578 26330706 C03221 15471 CPD-7222 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 Struijk, Cornelia B.; Beerthuis, R. K. The enzymic conversion of 3cis-and 3trans-alkenoyl-CoA esters into their 2trans-isomers. Biochimica et Biophysica Acta, Lipids and Lipid Metabolism (1966), 116(1), 12-22. Fatty acid oxidation complex subunit alpha P21177 FADB_ECOLI fadB http://ecmdb.ca/proteins/P21177.xml Probable enoyl-CoA hydratase paaF P76082 PAAF_ECOLI paaF http://ecmdb.ca/proteins/P76082.xml Fatty acid oxidation complex subunit alpha_ P77399 FADJ_ECOLI fadJ http://ecmdb.ca/proteins/P77399.xml Acyl-coenzyme A dehydrogenase Q47146 FADE_ECOLI fadE http://ecmdb.ca/proteins/Q47146.xml Fatty acid oxidation complex subunit alpha P21177 FADB_ECOLI fadB http://ecmdb.ca/proteins/P21177.xml (S)-3-Hydroxydodecanoyl-CoA <> (2E)-Dodecenoyl-CoA + Water R04170 Lauroyl-CoA + FAD <> (2E)-Dodecenoyl-CoA + FADH2 R03857 (2E)-Dodecenoyl-CoA > Water + (S)-3-Hydroxydodecanoyl-CoA PW_R003783 (3Z)-Dodec-3-enoyl-CoA > (2E)-Dodecenoyl-CoA PW_R003782